合成路线:The acylation of 2,3-dihydrobenzofuran (I) with acetyl chloride and AlCl3 in dichloromethane gives 5-acetyl-2,3-dihydrobenzofuran (II),which by reaction with sulfur,morpholine (III) and p-toluenesulfonic acid at high temperature yields 2-(2,3-dihydrobenzofuran-5-yl)thioacetic acid morpholide (IV).The hydrolysis of (IV) with H2SO4 in refluxing water-acetic acid affords 2-(2,3-dihydrobenzofuran-5-yl) acetic acid (V),which is esterified to (VI) with ethanol and H2SO4 in refluxing toluene.The condensation of the ester (VI) with 4-(methylthio)benzoyl chloride (VII) by means of SnCl4 in refluxing dichloromethane gives ethyl 2-[7-[4-(methylthio)benzoyl]benzofuran-5-yl]acetate (VIII),which by hydrolysis with NaOH in refluxing methanol-water yields the corresponding acid (IX).Finally,this compound is dehydrogenated with N-bromosuccinimide (NBS) and dibenzoyl peroxide in refluxing CCl4.
参考文献标题:TIFURAC SODIUM < Rec INNM; USAN >
文献作者:Prous,J.; Castar,J.
参考来源:Drugs Fut 1989,14(8),775
合成路线:The acylation of 2,3-dihydrobenzofuran (I) with acetyl chloride and AlCl3 in dichloromethane gives 5-acetyl-2,3-dihydrobenzofuran (II),which by reaction with sulfur,morpholine (III) and p-toluenesulfonic acid at high temperature yields 2-(2,3-dihydrobenzofuran-5-yl)thioacetic acid morpholide (IV).The hydrolysis of (IV) with H2SO4 in refluxing water-acetic acid affords 2-(2,3-dihydrobenzofuran-5-yl) acetic acid (V),which is esterified to (VI) with ethanol and H2SO4 in refluxing toluene.The condensation of the ester (VI) with 4-(methylthio)benzoyl chloride (VII) by means of SnCl4 in refluxing dichloromethane gives ethyl 2-[7-[4-(methylthio)benzoyl]benzofuran-5-yl]acetate (VIII),which by hydrolysis with NaOH in refluxing methanol-water yields the corresponding acid (IX).Finally,this compound is dehydrogenated with N-bromosuccinimide (NBS) and dibenzoyl peroxide in refluxing CCl4.
参考文献标题:Analgetic and antiinflammatory 7-aroylbenzofuran-5-yl acetic acids and 7-aroylbenzothiophene-5-ylacetic acids
文献作者:Tomolonis,A.J.; Dunn,J.P.; Ackerman,N.A.
参考来源:J Med Chem 1986,29(11),2326
产品链接: CAS No. 102488-97-1›› 产品链接: CAS No.97483-17-5››